Vacation rentals with a pool in Charlottesville

18th Century Charming Bungalow #127 Pool & Spa

Escape & unwind from city life on a beautiful historic, 250 acre estate 20 minutes from Charlottesville! Our historic bungalow is perfect for those who want to take a step back in history and enjoy the wonder nature has to offer! Steep stairs access the upstairs bedroom, 2 can sleep downstairs. We are only 20 min away from Jefferson's "Monticello" & from James Madison's " Montpelier". Treat yourself to an onsite certified massage with a wellness therapist.Please book online at Spagreensprings.

Mountain Cottage, Pool , Views, Wine / Brew Trail

Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

Private Apt in Historic C'ville Home (Garden Side)

This cozy, newly refurbished, 1 BR/1 Bath, apartment is attached to a historic Charlottesville home. With just a 10 min walk to the Downtown Mall and a short drive to the university hospital/campus, the location is nestled in the heart of C'ville. Special amenities include a Sleep Number bed, fast Wifi, a 50" Smart TV with access to Amazon Prime and Netflix, access to pool use during the summer, and Park Lane street parking. Hand crafted soapstone counters and farm sink, beautiful new tile work.

Jefferson Cottage quiet farm close to everything

The cottage circa 1802 offer a peaceful private setting on a historic horse farm once part of Monticello with close proximity to wineries (10 minutes), town (12 minutes), Rivanna River borders the property, Carter mountain (8 minutes) and many other activities. A "Jimmy Buffet" salt water pool complex has a private Jacuzzi for each unit, double bars, two fire pits, frig ,full bath/shower/changing room) There is a private lake (catch and release fishing) and many places to walk on the property.

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Yurt*POOLpeace*FARM*horses*goats*woods*STARS*Hotub

Come experience living in a round structure filled with amenities-fully equipped kitchen, deep tub, heating and AC, hot tub and in-ground pool. Great for couples, friends, and families. A 10 minute hike gets you into Shenandoah National Park, explore our 58 acres on numerous walking trails, visit Charlottesville, historical sites, caves, or play in rivers. Child friendly- no pets.( PRIVATE hot tub Nov 1- March 1.) Check out Cair Paravel Farmstead on FB/the web to see all we have to offer

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

Mountain View Nest

From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

Romantic, Carriage House Studio at Fairhill Farm

Delight in the bold views of the Blue Ridge Mountains while lounging on your private deck at the Carriage House on Fairhill Farm. Stroll on 150 acres. Hike our private trails. Fish in private pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Located 2 hours southwest of Washington, DC, 1 1/2 hours east of Richmond and 25 minutes north of Charlottesville, VA. Near Shenandoah National Park, Monticello, Montpelier, Ash Lawn, and UVA

Mountaintop Overlook: Warm Fires • Golden Views

Breathe in the Crisp Air, Cozy Up by the Fire, Take in Golden Views. The Mountain Top Overlook @ Wintergreen Resort is a cozy and clean two bedroom(king size beds), two full bathroom condo with a living room sleeper sofa. This condo accommodates 6 guests. It boasts panoramic window views of the Blue Ridge Mountains, while being located in sought after Wintergreen Resort. Ground level with easy access off the deck to a grassy area overlooking the valley.